When Hell Comes AKnockin'
by everythingyouwantt
Summary: Continuation of Once a Winchester, Always a Winchester: Dean's been sent off to hell and when he comes back, he is placed in between a very guilty looking brother and heartbroken sister. Dean's also not the only one that Heaven has a plan for...
1. Where's Heaven Now?

**Author's Notes: Yay for starting the next part! This takes part shortly after Dean is taken off to Hell. If you have not read my first story a simple background is that Olivia is a sister to the Winchester brothers. Personally, I think reading the first part is necessary because you see how they bond and interact and you know Olivia's character. Things have gotten serious in this part of the story, so I hope you enjoy it! Feedback is appreciated!**

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**A knock echoed through Bobby Singer's home. He sat, rather stationary, at the table in his kitchen. Whiskey bottles, most of the empty, sat clumped together on the table. Books laid out open, revealing the months' worth of research. He held a shot glass in his hand, twirling the liquid in the glass. He had consumed so much alcohol in the past seven days that it was a wonder he was still functioning properly. Though, functioning wouldn't really describe Bobby these past few days. The alcohol consumption and lack of sleep wore the poor man down. How exactly was he going to do this?

Another knock on the door echoed. Bobby sighed. Olivia was just not use to the fact that knocking and coming in was acceptable to him. "Come in!" he yelled from the table and downed the shot he had in his hand.

His eyes fell upon the Winchester sister. Her dark brown hair cut a few inches shorter since he saw her eight days ago. The shorter hair had sprung up in spirals of pretty curls. Her bright brown eyes stared at him doe-like. He always thought her outfits were a little too classy for the hunts she was involved in. Usually nice jeans with a form-fitting top and jacket were her common attire and a pair of black boots. Though she looked nicer than the boys every looked, she never complained when she got something on the outfit. Maybe she had picked that attitude up from her brothers that they were simply articles of clothing and not to be fussed over.

Her eyes fell upon the bottles of alcohol and then looked to him. He wasn't ready for that look. Heartbrokenness rimmed those bright eyes. Her voice was just a whisper when she spoke, "Bobby, what's going on?" she asked. He watched Olivia as she took a deep breath to ease her frayed nerves. "Neither of them is picking up their phones. I hear from them every week…" she shook her head in confusion to her brothers' absences. She was right. Dean made a point to contact her every week and visit when possible when she decided to stay stationary about 25 miles away from Bobby himself to hone her skills and earn a little money before continuing with her brothers on the hunts.

Bobby took a deep breath, "To be honest, I only know where one of your brothers is…" He knew exactly where Dean was, body and soul. Sam, well, he hadn't heard from Sam since they…Bobby's jaw clenched. He couldn't even think about it and he had to tell Olivia about Dean.

"One?" she said. He heard her exhale sharply. Her bottom lip quivered. She wasn't a stupid girl, she was very intelligent and Bobby could see her putting the pieces together in that sharp mind of hers. Her teeth chattered a little as she tried to speak, "Which?" she finally got out. Her lips were parted because she could no longer intake enough air through her nose. She waited for Bobby to seal her fate.

"Dean."

Bobby could feel the tears begin to bubble up like they had been. He saw Olivia lose her footing and slide down the doorway to the kitchen. "Is that why Sam won't answer his phone? Is that why he won't talk to me? What happened? When you three visited me last week, everything was fine…" her words drifted as she looked at Bobby. He drearily shook his head towards her.

"No, sweetheart, everything was far from fine." Bobby cleared his throat and told her the story of how Sam had been killed and Dean sold his soul for Sam's return. "They didn't tell you, because those boys are pigheaded. They thought they were going to beat this deal and they fought it until the clock struck midnight…."

He watched as Olivia's whole world was torn at the seams, "Sold his soul?" she whispered. "So my brother's soul is hell? Dean's suffering for an eternity….in hell?" she whispered. The tears were cascading down her cheeks. The whole reason she stayed behind her brothers was to get better. Olivia felt like a liability to Dean and Sam and now that plan had been burned in a fire.

Bobby could hardly watch as Olivia broke down. Her sobs were so hard that she could breathe. The sound she made sounded like she was almost in physical pain. The thought of her brother suffering was too much to bear. Bobby remembered watching Sam cry and maybe Olivia just put what he was feeling in better perspective. Sam became vengeful and soon tears would not suffice, which was why Bobby had not heard from the younger brother. Olivia, however, just let out the hurt and did not let it become vengeful. Instead, she felt helpless and pitiful for her brother trapped forever in hell's grasp.

Bobby had had enough of Olivia's display on the floor. He wiped away the tears that had managed to spill over and walked over to Olivia. He helped the poor girl up and got her to the couch. He sat next to her and just let her cry on his shoulder. He wrapped an arm around her shoulders and ran his hand lightly over them. This motion wouldn't ease her, not in the slightest, but it would let her know that he wasn't leaving her.

Hours had passed and the afternoon sun had faded behind the horizon. Bobby ordered pizza, yet again, because he didn't feel like cooking and Olivia didn't either. He stood by the door waiting for the pizza to arrive while watching Olivia. She had been pacing back and forth in the same five feet stretch of carpet with her cell phone to her ear. She called nearly every phone number those boys would have, but never having an answer. She always had to leave a message for Sam, pleading for him to call her and how she knew what happened and how much she could really use him and she knew he needed her.

They ate in silence. Bobby sat watching Olivia. Olivia sat watching her cell phone, just waiting for it to ring. Bobby stood up to throw his plate away when Olivia first spoke up, "Did you burn his body?" she asked. Her voice was weary and she was clearly still battling between calm and breaking into tears again. Bobby looked up at her and shook his head, "No, Sam demanded we bury him."

Bobby was surprised by Olivia's next question. "Can I go see him?" she questioned. Seeing his grave would make it official that he was gone. However, Bobby could see the determination in her eyes to see her brother's grave. He nodded, "Yes, you can see him…"

Olivia hiked through the grasses behind Bobby until they got to a forested area. Bobby pointed ahead, "He's straight ahead. I figure you will want to talk to him alone…" Olivia nodded and took her flashlight and went straight like Bobby had told her. In a small clearing, a wooden cross sat. Olivia felt her heart pound against her rib cage, but she continued.

She kneeled down before the cross. It was highlighted in silver light from the moon. Olivia sat calmly for a few seconds before becoming frantic. She began to dig at the dirt with her bare hands. Her mind racing with how it couldn't be true that Dean was in the ground and she had to see it for herself. She frantically dug into the earth, gasping and crying. She calmed down after only a few moments, looking at her dirty hands. It was a ridiculous act and the more ridiculous she knew she was acting the more she realized there was nothing she could do to disprove that her brother's body wasn't down in the grave. The realization came crashing down and she sobbed more.

Olivia could feel the dirt sticking to her skin on her face and hands. She had laid down on the dirt and grass. Her hair stuck to her face from her cheeks being soaked with tears. "Dean…?" Her whisper carried out into the darkness. "You probably can't even hear me…" she said, shaking her head, "But maybe you can…" She sighed and sat up on the ground. Her hand ran over the ground to remove her digging marks.

"We need you….Sam, Bobby, me…" She said lightly. She paused, her lip trembled as she spoke. "I knew…I knew this was going to happen Dean and….I didn't stop it….Dean, what do I do? If this is actually happening, then Sam's going to the evil side and he won't pick up his phone so I don't even know if he is alright now. For all I know Lucifer could have taken him as a vessel already…" Olivia began choking nearly on her sobs as she spoke into the night again. "Sam won't listen to me. He will listen to you. He looks up to you. He needs you, Dean. I need you. I need you to be my rock again, because everything is falling apart and you were always the one to help fix it…."

She sat with her head inclined to look at the tree tops. "That demon said that you were on Heaven's side….Where's Heaven now!?" her voice became sharp and shrill, scaring a few birds from the tree tops.

She reached up with the sleeve of her jacket to remove the tears from her cheeks. Olivia hardly cried anymore these days. It was only because of her brothers, like when they would leave after visiting her, she would shed tears.

The youngest Winchester had crumpled to the ground again, "What am I suppose to do Dean..?" she whispered. "How am I suppose to keep going? You and Sam and Bobby are that I have left in their world…" She winced at how true it was. Again, she sat up and dusted herself off. She stood up from the grave and sighed, reaching up to wipe away the tears. She slowly walked away from the grave, but her arms stayed around her body, holding her torso. Tears still rolled down her cheeks.

Olivia walked back into Bobby's home to find the old man sprawled out on the couch. Olivia walked to the bathroom. "God…I look like hell…" she muttered as she stared into the mirror. Dirt was spread across her face while she tried to wipe away the tears. She cleaned her face and hands and ran her fingers through her hair. At least she didn't look like she had been trekking some monstrous back woods path like she did previously.

She walked back to the couch and jostled Bobby awake lightly. He snored lightly and woke himself sitting up on the couch, "Wha? What's the matter?" he asked, taking hold of Olivia's arm. "Nothing…" she said lightly. "Well then why did you wake me up? You get my bed. I changed the sheets and everything…" Olivia put her hands on hips, "Robert Singer you know damn well that I don't kick you out of your bed. Go to bed. I can sleep on the couch. It's fine…."

Bobby watched the look in her eyes and nodded, not wanting to fight with her. "Fine…lady gets the lumpy couch…" He got up with a groan and Olivia guided him forward a little. She grabbed her bag and took out a t-shirt and boxer shorts for pajamas. After she changed and did all the "before bed to-dos" she curled up on the couch with a knitted blanket. Sleep came fast since crying had taken so much energy.


	2. It's Not What He Wanted

**Author's Notes: Chapter 2 =] I'm seriously loving how this is unfolding. I personally love Olivia's character and not just because she is a character I created, but she is the voice of reason between the brothers and she really cares for her brothers. Anyway, here's the next chapter! Feedback appreciated!**

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**A week had past slowly while Olivia stayed with Bobby. She went to work at the local restaurant when she was scheduled to work. The rest of the time Bobby watched her as she wasted away on the couch. She would stare blankly at the tv and Bobby had to shake her so that she would come to dinner, otherwise she wouldn't move to eat.

One night, Olivia laid on the couch, staring up at the ceiling. Hours had passed since Bobby had headed to bed, so it was probably around 3 in the morning. Her phone vibrated on the table. She looked over at it and lazily picked it up, expecting a drunk person misdialing her number. When she saw the caller ID, she snapped her phone open, "Sam?"

Olivia stood outside the motel and took a deep sigh. Room 11, that's what he said, right? She walked up to the door and raised her fist to knock. She noticed how much her hand trembled. She knocked on the door and then pulled her hand away to try and calm her nerves.

A dark haired woman answered the door. Her dark eyes fell on Olivia and Olivia suddenly felt guilty. "I'm sorry….I must have gotten the wrong…." Olivia's eyes set on Sam standing in the back. "Let her in," Sam said. The woman looked at Olivia, almost glaring, and then moved out of the way.

Olivia felt her eyes tear up as she walked through the doorway. Sam was right in front of her completely, perfectly fine. She couldn't ask for a better gift. Sam looked past her at the woman, "Can you excuse for a few moments?" he asked. Olivia turned to the woman, who narrowed her eyes at Olivia, but obliged to Sam and grabbed a jacket and went outside.

"Olivia, I'm so sorry about now answering your calls…" Sam said after the door closed. Olivia turned to her brother, "It-it's okay…" she muttered. Sam walked up to her and grabbed her shoulders. "No, it's not. Especially with what we have been going through, I shouldn't have left you alone…" Olivia looked up at her brother, noticing his dilated eyes and how his hands shook a little on her shoulders. Apparently, Olivia's face had twisted into a quizzical expression because Sam then suggested they sit down on the beds in the room.

"Who was that woman?" Olivia asked. She watched as Sam became uneasy, "Just a girl," he replied. The female Winchester's eyes narrowed, "You're lying to me…Sam, I'm not stupid. Being with you and Dean, I know your mannerisms pretty well…" Olivia was surprised at her herself for being able to say Dean's name so easily. She watched as Sam became even more unsettled.

Sam took a deep breath, "That's Ruby…" he finally said. "Dean said she was a blonde…" Olivia said, trying to keep an even tone while she spoke. Sam informed her that Ruby lost her original host when they were fighting with Lilith and she had taken a host in a comatose patient. Olivia nodded slightly, "Why…why are you with her?"

The phone conversations she had with Dean came back into her memory. She could vividly remember Dean's disgust when he said Ruby was helping them. The distrust in his voice was quite obvious. He told her they were using her and then disposing of her. Bobby had said something to her over the past week about Ruby and how she said she could help Dean. She had obviously failed quite pitifully.

"She's helping me to get rid of Lilith, since that's all I can do…" Sam said. Olivia's eyes narrowed, "How so, Sam?" "She's just helping me…" Sam said. Olivia stood up off the bed, "How Sam?" She leaned into her brother, "Your pupils are dilated and you're shaking…Has she given you something?" She grabbed her brother's chin, examining his eyes.

Sam looked almost appalled when his sister came to the conclusion and pulled his chin from her grasp. "No," he said, "That's not how she's helping me. You think she's drugging me up?" Olivia paused and stared at Sam. His face said angry, but his eyes said guilty.

"You're still lying to me…" Olivia whispered and fell back upon the bed. Tears began bubbling over in her eyes again. "Sam, you are all I have now. Did you listen to my messages? Did you know that my mom died in a car crash? Did you know I've been sleeping on Bobby's couch for the past week, because I can't bring myself to be alone? If you won't talk to me, who will you talk to? I need you to let me in…."

Sam brought his eyes to Olivia's, looking pitiful. He had listened to her messages. Every single one. But he knew it would come down to this moment and he was still unsure of how to break it to his sister. He took his sister's hands. She was right, they were trembling and hers felt so steady in his. "I've been drinking demon blood to make my psychic powers stronger. If I get stronger, I can take on Lilith…"

Olivia's eyes fell from her brother's. Demon blood? She tore away from her brother's hands and paced along the bottom of the edges of the beds. "Demon blood, Sam? How is that going to help? Sam, taking in demon blood…It looks like it acts like a drug…It's gonna alter your personality. It could kill you, do you understand that?"

"I can get rid of Lilith then and maybe then I can get Dean out of hell. It's what we both want. We both want Dean back," Sam said.

"I don't want one back at the cost of another!" Olivia cried. Tears were streaming down her face. The description of hurt didn't even begin to cover what she was feeling towards her brother right now. Her body shook from all her unsteady emotions. She placed her face in her hands.

Sam got up and went to his sister. He brought her into his arms and hugged her closely. "I don't wanna lose you both…please….stop…." she whispered into her brother's chest. Sam winched, knowing he couldn't stop. He had to do this. If he couldn't get Dean back, then the least he could do was kill the demon who sent him to Hell.

Olivia stepped away from Sam. "You won't stop will you?" she asked. Sam shook his head. "This could kill you! Why don't you understand?! I need at least one of my brothers! If this continues, it will kill you! You will lose yourself to the darkness! Sam, you will become what we hunt!" Olivia's sobs were becoming louder and louder.

"I'm doing this for Dean!" Sam said. "For Dean?!" Olivia cried, becoming furious that Sam would use their brother's memory as an excuse to continue. "He wouldn't want this! How does consuming demon blood help anyone?!" Olivia stomped to the door, "Let me know when you find something reasonable to remember our brother by and when you dump Demon Bitch…" and slammed the door shut behind her.

Sam fell on to the bed. His hand sat on his forehead. Maybe this wasn't the right thing to do. He heard the door open and the bed sink next to him. "You will be helping your brother. You'll see…" he heard Ruby croon.

Olivia stomped to her car. She thought for sure she wouldn't be able to cry for months because of all the crying she had done for Dean. She thought she would be out of tears for sure, but clearly she still had tears.

"Olivia?" The Winchester sister gasped and turned. Behind her was a young woman, probably only a couple years older than Olivia herself. Her voice was soft and light. She had pretty blonde curls around her face and very pale, fragile looking skin. "Who are you?" Olivia asked, wiping away her tears.

"My name is Azrael. I'm the angel of death and Heaven needs your help…" she said softly.


	3. Lazarus Rising

**Guys Please Comment! I don't want to be writing to an empty crowd! Thanks so much!**

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God, even in September South Dakota had some wicked heat. Olivia lounged in the small home she was able to afford. She really didn't even want to move from the couch and with no work assignment at the bar, she was stuck at home. The air conditioning of course was busted, leaving nothing but the stiff breezes to come in through the open windows.

The female Winchester rolled to her side, hearing her cell phone ring on the table in the dining room where she left it. With a sigh, she rolled completely off the couch and on to her knees from there she got up and went into the dining room. "Bobby?" she questioned, seeing his caller id on the screen. "Are you home?" he asked. "Yeah…" Olivia said, wondering where the conversation was going. "Well, let us in, because we're coming up on your porch…" and the line went dead.

Olivia hung up her phone. Who was 'we?' Unless Sam started talking to Bobby, but from her knowledge he hadn't. She set down her cell phone and went to the door, "Bobby, what are you talking about?" she asked, but fell silent immediately. She now understood why Bobby said 'we.'

"Hey Olivia," Dean said, as casual as could be, like when he would visit her once a week or so back when he was alive. But that didn't make sense, because he was alive now, standing right next to Bobby. Olivia's breath quickened as if she had just finished running up a few flights of steps. She stumbled backwards in to her house and was quick to grab the pistol she always kept by the door. She aimed it at Dean. It couldn't be him. Bobby had told her he was dead, sent to hell to keep Sam alive.

Dean quickly put his hands up, "Whoa, whoa, whoa. Olivia, it's me." Dean's voice was calm and slightly convincing. Olivia's hand trembled as she held the pistol, but she pushed down the hammer, making it ready to shoot. "Olivia, it's him!" Bobby cried.

Olivia turned to Bobby, never removing her aim from Dean. There were tears in her eyes as she looked to Bobby, "You said he was dead! You said he had been taken to Hell! If that's true, then he shouldn't be here now!" she cried. Bobby was taken aback by her cries. "I know, sweetheart. I don't know how this happened either, but it's really him…" Olivia looked back to Dean. Her face began to crumple in tears and she lowered her gun, "Is it really…?" she asked through the tears. Dean nodded, "It's really me, little sister…"

Olivia put the hammer back on her gun and set it on the table by the door. She walked out of the doorway and down the steps. Dean took her into his arms, allowing her to cry. "I missed you…" she sobbed, "I missed you so much…" Dean placed his lips to the top of her head, "I missed you too…" he said, a light laugh escaping his lips.

"I haven't seen Sam in like a week," Olivia said. They had moved into her kitchen area. Bobby and Dean were sitting at the table while Olivia poured Dean a glass of water. "Well, I haven't seen him since Dean went to Hell, so you've seen him last," Bobby said. Olivia's brow furrowed, "He hasn't talked to you for four months?" she asked, handing Dean the glass of water. Bobby shook his head. "Dammit Sam…" she muttered.

Olivia went into the living room and grabbed her cell phone. She flipped it open and pressed 2 on her speed dial. She listened as the phone rang, and heard the phone click. "Hello?" she heard Sam ask. "Sam! Where are you? I think I may have a job…" Olivia said, sounding very convincing. Dean went to reach for her phone, but Olivia put her hand up and then twisted on her heels away from her eldest brother. She went over to a pad and pen and wrote down the Illinois address and the room number before bidding her brother goodbye.

She turned and handed the piece of paper. "Well now we have specifics other than just the town from the GPS on his phone," Dean said, taking the piece of paper from his sister's hand. He got up and headed to the door with Bobby at his side. "Let me go with you," Olivia said, reaching to grab her keys but Dean shook his head. "This may get ugly. We think Sam made a deal…" Dean said, pulling her hand away from her keys. Olivia's brow furrowed, "So you're just going to leave me out again of another demon deal?" she asked.

Dean swallowed hard against his throat. He had left Olivia out of his deal, because everyone knew and pitied him. He didn't want to see that look in his sister's eyes. "Look…we will come back for you. I will call you as soon as we talk to him. I promise…" Dean took his sister in his arms again, "I promise. I won't leave you out this time." He released her and walked out to door to Bobby's car. Olivia walked to the window and watched the car leave in a hurry.

"I thought it would be better to not inform you about your brother's return…" Olivia turned to look at Azrael. "You did this?" she asked. Azrael shook her head, "I did not. One of my brother's did, but yes, Dean was pulled from Hell by an angel." Olivia breathed a sigh of relief. There was not another demon deal hovering over their heads.

"Olivia….you told me you would speak to your brother. He needs to stop," Azrael said, her tone getting terse. "I've tried. Besides, he's not doing it as much. He's helping people, keeping them alive. I don't understand why it's so terrible…" Olivia said lightly. After Sam and her had their harsh argument, she gave into Sam's begging to go on a hunt with her. She saw how he was able to keep them alive and it was quicker than reciting a book in Latin. She trusted Sam's judgment, but Olivia still didn't trust Ruby.

Azrael shifted the weight upon her feet, "It is unnatural, Olivia. Terrible things will come of it…" Olivia's eyes bore into Azrael, "What things?" she asked, but the angel disappeared. Olivia's face soured, that angel never told her anything in a clear manner. She would tell her enough that more questions were raised than answers.


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